# Supplementary Information (SI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3
_database_code_depnum_ccdc_archive 'CCDC 2304097'
loop_
_audit_author_name
_audit_author_address
'Li Li'
;Henan Polytechnic University
China
;
_audit_update_record             
;
2024-07-29 deposited with the CCDC.	2024-10-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C54 H44 N4 O19'
_chemical_formula_weight         1052.93

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.9394(15)
_cell_length_b                   17.884(2)
_cell_length_c                   19.2029(17)
_cell_angle_alpha                90
_cell_angle_beta                 94.343(3)
_cell_angle_gamma                90
_cell_volume                     4773.4(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    4288
_cell_measurement_theta_min      2.7085
_cell_measurement_theta_max      24.2715

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_F_000             2192
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.113
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34405
_diffrn_reflns_av_unetI/netI     0.0955
_diffrn_reflns_av_R_equivalents  0.1231
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.738
_diffrn_reflns_theta_max         25.060
_diffrn_reflns_theta_full        25.060
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             8399
_reflns_number_gt                4336
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0886P)²+4.8638P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8399
_refine_ls_number_parameters     700
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1631
_refine_ls_R_factor_gt           0.0747
_refine_ls_wR_factor_ref         0.2126
_refine_ls_wR_factor_gt          0.1670
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1074(4) 1.4158(3) 0.4726(2) 0.0512(13) Uani 1 1 d . . . . .
H1A H 0.095321 1.419344 0.424374 0.061 Uiso 1 1 calc R U . . .
C2 C 0.1022(3) 1.3460(3) 0.5032(2) 0.0441(12) Uani 1 1 d . . . . .
H2 H 0.087881 1.303996 0.475810 0.053 Uiso 1 1 calc R U . . .
C3 C 0.1183(3) 1.3393(2) 0.5745(2) 0.0316(10) Uani 1 1 d . . . . .
C4 C 0.1411(4) 1.4046(3) 0.6111(2) 0.0484(13) Uani 1 1 d . . . . .
H4A H 0.153272 1.403103 0.659390 0.058 Uiso 1 1 calc R U . . .
C5 C 0.1456(4) 1.4713(3) 0.5762(2) 0.0514(13) Uani 1 1 d . . . . .
H5 H 0.161408 1.514294 0.601864 0.062 Uiso 1 1 calc R U . . .
C6 C 0.1158(3) 1.2666(2) 0.6107(2) 0.0316(10) Uani 1 1 d . . . . .
C7 C 0.1352(3) 1.2002(2) 0.5770(2) 0.0335(10) Uani 1 1 d . . . . .
H7 H 0.145034 1.200399 0.529671 0.040 Uiso 1 1 calc R U . . .
C8 C 0.1400(3) 1.1347(3) 0.6135(2) 0.0369(11) Uani 1 1 d . . . . .
H8A H 0.154054 1.090621 0.590710 0.044 Uiso 1 1 calc R U . . .
C9 C 0.1024(3) 1.1951(3) 0.7150(2) 0.0423(12) Uani 1 1 d . . . . .
H9 H 0.090186 1.193079 0.761866 0.051 Uiso 1 1 calc R U . . .
C10 C 0.0972(3) 1.2620(2) 0.6806(2) 0.0383(11) Uani 1 1 d . . . . .
H10 H 0.080994 1.305041 0.704272 0.046 Uiso 1 1 calc R U . . .
C11 C 0.1400(3) 1.0622(3) 0.7213(2) 0.0427(12) Uani 1 1 d . . . . .
H11A H 0.106806 1.021529 0.696247 0.051 Uiso 1 1 calc R U . . .
H11B H 0.114087 1.066926 0.766563 0.051 Uiso 1 1 calc R U . . .
C12 C 0.2461(3) 1.0458(2) 0.7306(2) 0.0372(11) Uani 1 1 d . . . . .
C13 C 0.2846(3) 0.9826(3) 0.7033(2) 0.0450(12) Uani 1 1 d . . . . .
H13 H 0.244241 0.948533 0.679049 0.054 Uiso 1 1 calc R U . . .
C14 C 0.3833(3) 0.9685(3) 0.7113(2) 0.0452(12) Uani 1 1 d . . . . .
H14 H 0.407641 0.925432 0.691984 0.054 Uiso 1 1 calc R U . . .
C15 C 0.4457(3) 1.0177(2) 0.7479(2) 0.0365(11) Uani 1 1 d . . . . .
C16 C 0.4057(4) 1.0811(3) 0.7750(3) 0.0507(13) Uani 1 1 d . . . . .
H16 H 0.445719 1.115247 0.799477 0.061 Uiso 1 1 calc R U . . .
C17 C 0.3086(4) 1.0952(3) 0.7668(2) 0.0503(13) Uani 1 1 d . . . . .
H17 H 0.284356 1.138440 0.785742 0.060 Uiso 1 1 calc R U . . .
C18 C 0.5501(3) 1.0008(2) 0.7584(2) 0.0367(11) Uani 1 1 d . . . . .
C19 C 0.5869(4) 0.9318(3) 0.7404(3) 0.0597(15) Uani 1 1 d . . . . .
H19 H 0.544668 0.895290 0.722178 0.072 Uiso 1 1 calc R U . . .
C20 C 0.6835(4) 0.9157(3) 0.7485(3) 0.0619(15) Uani 1 1 d . . . . .
H20 H 0.705262 0.869148 0.735005 0.074 Uiso 1 1 calc R U . . .
C21 C 0.7485(3) 0.9677(3) 0.7763(2) 0.0411(11) Uani 1 1 d . . . . .
C22 C 0.7135(3) 1.0367(3) 0.7948(2) 0.0424(12) Uani 1 1 d . . . . .
H22 H 0.755950 1.072804 0.813695 0.051 Uiso 1 1 calc R U . . .
C23 C 0.6161(3) 1.0528(3) 0.7856(2) 0.0410(11) Uani 1 1 d . . . . .
H23 H 0.594590 1.099841 0.798031 0.049 Uiso 1 1 calc R U . . .
C24 C 0.8545(3) 0.9513(3) 0.7851(2) 0.0447(12) Uani 1 1 d . . . . .
H24A H 0.880242 0.948431 0.739600 0.054 Uiso 1 1 calc R U . . .
H24B H 0.887407 0.991421 0.811169 0.054 Uiso 1 1 calc R U . . .
C25 C 0.8814(4) 0.8165(3) 0.7872(2) 0.0498(13) Uani 1 1 d . . . . .
H25 H 0.884951 0.818605 0.739050 0.060 Uiso 1 1 calc R U . . .
C26 C 0.8870(4) 0.7486(3) 0.8201(2) 0.0452(12) Uani 1 1 d . . . . .
H26 H 0.892303 0.705181 0.794076 0.054 Uiso 1 1 calc R U . . .
C27 C 0.8847(3) 0.7442(2) 0.8920(2) 0.0318(10) Uani 1 1 d . . . . .
C28 C 0.8768(3) 0.8106(2) 0.9277(2) 0.0370(11) Uani 1 1 d . . . . .
H28 H 0.876656 0.810291 0.976153 0.044 Uiso 1 1 calc R U . . .
C29 C 0.8691(3) 0.8770(2) 0.8921(2) 0.0391(11) Uani 1 1 d . . . . .
H29 H 0.862262 0.921142 0.916734 0.047 Uiso 1 1 calc R U . . .
C30 C 0.8858(3) 0.6703(2) 0.9273(2) 0.0330(10) Uani 1 1 d . . . . .
C31 C 0.9118(5) 0.6065(3) 0.8952(3) 0.0729(19) Uani 1 1 d . . . . .
H31 H 0.934510 0.608888 0.850954 0.087 Uiso 1 1 calc R U . . .
C32 C 0.9049(5) 0.5382(3) 0.9277(3) 0.0720(18) Uani 1 1 d . . . . .
H32 H 0.921749 0.495621 0.903621 0.086 Uiso 1 1 calc R U . . .
C33 C 0.8538(4) 0.5914(3) 1.0228(3) 0.0645(16) Uani 1 1 d . . . . .
H33 H 0.834443 0.587092 1.067927 0.077 Uiso 1 1 calc R U . . .
C34 C 0.8575(4) 0.6624(3) 0.9940(2) 0.0557(14) Uani 1 1 d . . . . .
H34 H 0.841089 0.704121 1.019394 0.067 Uiso 1 1 calc R U . . .
C35 C 0.1318(3) 0.7599(2) 0.41739(18) 0.0272(9) Uani 1 1 d . . . . .
H35 H 0.142629 0.722485 0.385296 0.033 Uiso 1 1 calc R U . . .
C36 C 0.1271(3) 0.7413(2) 0.48732(19) 0.0280(9) Uani 1 1 d . . . . .
C37 C 0.1115(3) 0.7976(2) 0.53570(18) 0.0289(10) Uani 1 1 d . . . . .
C38 C 0.0989(3) 0.8711(2) 0.51293(19) 0.0325(10) Uani 1 1 d . . . . .
H38 H 0.087229 0.908443 0.544947 0.039 Uiso 1 1 calc R U . . .
C39 C 0.1034(3) 0.8894(2) 0.44258(19) 0.0274(9) Uani 1 1 d . . . . .
C40 C 0.1206(3) 0.8335(2) 0.39445(18) 0.0262(9) Uani 1 1 d . . . . .
C41 C 0.1211(3) 0.8510(2) 0.3185(2) 0.0314(10) Uani 1 1 d . . . . .
C42 C 0.0865(4) 0.9697(2) 0.4229(2) 0.0341(10) Uani 1 1 d . . . . .
C43 C 0.0996(4) 0.7835(2) 0.6126(2) 0.0412(12) Uani 1 1 d . . . . .
C44 C 0.1386(3) 0.6621(2) 0.5103(2) 0.0352(10) Uani 1 1 d . . . . .
C45 C 0.1334(3) 0.7542(2) 0.91826(18) 0.0261(9) Uani 1 1 d . . . . .
H45 H 0.134536 0.715362 0.886152 0.031 Uiso 1 1 calc R U . . .
C46 C 0.1384(3) 0.7369(2) 0.98896(19) 0.0284(9) Uani 1 1 d . . . . .
C47 C 0.1435(3) 0.7956(2) 1.03750(18) 0.0310(10) Uani 1 1 d . . . . .
C48 C 0.1341(3) 0.8680(2) 1.0131(2) 0.0350(11) Uani 1 1 d . . . . .
H48 H 0.134933 0.906636 1.045523 0.042 Uiso 1 1 calc R U . . .
C49 C 0.1235(3) 0.8862(2) 0.94219(19) 0.0297(10) Uani 1 1 d . . . . .
C50 C 0.1266(3) 0.8272(2) 0.89348(19) 0.0284(10) Uani 1 1 d . . . . .
C51 C 0.1272(3) 0.8349(3) 0.8146(2) 0.0374(11) Uani 1 1 d . . . . .
C52 C 0.1093(3) 0.9690(3) 0.9278(2) 0.0414(12) Uani 1 1 d . . . . .
C53 C 0.1645(4) 0.7854(2) 1.1158(2) 0.0399(11) Uani 1 1 d . . . . .
C54 C 0.1320(3) 0.6576(2) 1.0125(2) 0.0370(11) Uani 1 1 d . . . . .
N1 N 0.1284(3) 1.4773(2) 0.50783(19) 0.0450(10) Uani 1 1 d . . . . .
N2 N 0.1248(2) 1.13249(19) 0.68170(18) 0.0341(9) Uani 1 1 d . . . . .
N3 N 0.8711(2) 0.87967(19) 0.82264(18) 0.0354(9) Uani 1 1 d . . . . .
N4 N 0.8761(3) 0.5298(2) 0.9902(2) 0.0446(10) Uani 1 1 d . . . . .
O1 O 0.1407(3) 0.61430(17) 0.45961(15) 0.0542(9) Uani 1 1 d . . . . .
H1 H 0.134873 0.571856 0.474888 0.081 Uiso 1 1 calc R U . . .
O2 O 0.1419(3) 0.64530(18) 0.57091(16) 0.0673(11) Uani 1 1 d . . . . .
O3 O 0.0214(3) 0.7674(2) 0.63246(17) 0.0689(11) Uani 1 1 d . . . . .
O4 O 0.1775(3) 0.7939(2) 0.65064(16) 0.0611(10) Uani 1 1 d . . . . .
H4 H 0.168187 0.785992 0.691633 0.092 Uiso 1 1 calc R U . . .
O5 O 0.0070(2) 0.99519(17) 0.41075(16) 0.0485(8) Uani 1 1 d . . . . .
O6 O 0.1655(3) 1.0088(2) 0.4250(2) 0.0717(12) Uani 1 1 d . . . . .
H6 H 0.152427 1.052624 0.416177 0.108 Uiso 1 1 calc R U . . .
O7 O 0.0965(3) 0.91129(18) 0.29527(15) 0.0558(10) Uani 1 1 d . . . . .
O8 O 0.1462(3) 0.79519(18) 0.28110(14) 0.0568(10) Uani 1 1 d . . . . .
H8 H 0.137865 0.805983 0.239579 0.085 Uiso 1 1 calc R U . . .
O9 O 0.1094(3) 0.8160(2) 1.15306(15) 0.0631(11) Uani 1 1 d . . . . .
O10 O 0.2392(3) 0.7540(2) 1.13715(16) 0.0729(12) Uani 1 1 d . . . . .
O11 O 0.1011(3) 0.64144(19) 1.06725(17) 0.0744(13) Uani 1 1 d . . . . .
O12 O 0.1574(3) 0.60860(16) 0.96742(15) 0.0489(9) Uani 1 1 d . . . . .
H12 H 0.145373 0.566444 0.981116 0.073 Uiso 1 1 calc R U . . .
O13 O 0.1592(3) 0.7817(2) 0.78275(15) 0.0623(10) Uani 1 1 d . . . . .
O14 O 0.0952(3) 0.89295(19) 0.78490(15) 0.0590(10) Uani 1 1 d . . . . .
O15 O 0.0753(3) 0.9901(2) 0.86699(18) 0.0733(12) Uani 1 1 d . . . . .
H15 H 0.078166 0.955302 0.839377 0.110 Uiso 1 1 calc R U . . .
O16 O 0.1263(3) 1.01415(19) 0.97403(19) 0.0690(11) Uani 1 1 d . . . . .
O17W O 0.9345(6) 0.6978(3) 0.1548(3) 0.169(3) Uani 1 1 d . . . . .
H17A H 0.979580 0.680459 0.132102 0.202 Uiso 1 1 d R U . . .
H17B H 0.922990 0.742347 0.141192 0.202 Uiso 1 1 d R U . . .
O18W O 0.9054(4) 0.8393(2) 0.1062(2) 0.1040(16) Uani 1 1 d . U . . .
H18A H 0.924808 0.871812 0.136347 0.125 Uiso 1 1 d R U . . .
H18B H 0.887187 0.862520 0.068967 0.125 Uiso 1 1 d R U . . .
O19W O 0.1418(3) 0.1503(2) 0.4020(2) 0.0758(12) Uani 1 1 d . . . . .
H19A H 0.184226 0.182280 0.392981 0.114 Uiso 1 1 d R U . . .
H19B H 0.088593 0.172729 0.393078 0.114 Uiso 1 1 d R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.312(6) . ?
C1 C2 1.384(6) . ?
C1 H1A 0.9300 . ?
C2 C3 1.375(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(6) . ?
C3 C6 1.476(6) . ?
C4 C5 1.373(6) . ?
C4 H4A 0.9300 . ?
C5 N1 1.321(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.389(6) . ?
C6 C10 1.388(5) . ?
C7 C8 1.364(6) . ?
C7 H7 0.9300 . ?
C8 N2 1.342(5) . ?
C8 H8A 0.9300 . ?
C9 N2 1.338(5) . ?
C9 C10 1.366(6) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 N2 1.476(5) . ?
C11 C12 1.505(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.373(6) . ?
C12 C17 1.390(6) . ?
C13 C14 1.395(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.391(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.382(6) . ?
C15 C18 1.486(6) . ?
C16 C17 1.374(7) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C23 1.383(6) . ?
C18 C19 1.389(6) . ?
C19 C20 1.374(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.377(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.384(6) . ?
C21 C24 1.503(6) . ?
C22 C23 1.386(6) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 N3 1.481(5) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 N3 1.332(6) . ?
C25 C26 1.369(6) . ?
C25 H25 0.9300 . ?
C26 C27 1.384(6) . ?
C26 H26 0.9300 . ?
C27 C28 1.381(6) . ?
C27 C30 1.485(6) . ?
C28 C29 1.371(6) . ?
C28 H28 0.9300 . ?
C29 N3 1.336(5) . ?
C29 H29 0.9300 . ?
C30 C31 1.360(6) . ?
C30 C34 1.375(6) . ?
C31 C32 1.378(7) . ?
C31 H31 0.9300 . ?
C32 N4 1.302(6) . ?
C32 H32 0.9300 . ?
C33 N4 1.317(6) . ?
C33 C34 1.388(7) . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
C35 C36 1.390(5) . ?
C35 C40 1.393(5) . ?
C35 H35 0.9300 . ?
C36 C37 1.398(5) . ?
C36 C44 1.489(6) . ?
C37 C38 1.392(6) . ?
C37 C43 1.520(5) . ?
C38 C39 1.396(5) . ?
C38 H38 0.9300 . ?
C39 C40 1.395(5) . ?
C39 C42 1.499(6) . ?
C40 C41 1.493(5) . ?
C41 O7 1.207(5) . ?
C41 O8 1.293(5) . ?
C42 O5 1.205(5) . ?
C42 O6 1.302(5) . ?
C43 O3 1.215(6) . ?
C43 O4 1.276(6) . ?
C44 O2 1.200(5) . ?
C44 O1 1.297(5) . ?
C45 C46 1.389(5) . ?
C45 C50 1.390(5) . ?
C45 H45 0.9300 . ?
C46 C47 1.403(5) . ?
C46 C54 1.493(6) . ?
C47 C48 1.379(6) . ?
C47 C53 1.521(5) . ?
C48 C49 1.397(5) . ?
C48 H48 0.9300 . ?
C49 C50 1.413(5) . ?
C49 C52 1.517(6) . ?
C50 C51 1.522(5) . ?
C51 O13 1.232(5) . ?
C51 O14 1.250(5) . ?
C52 O16 1.210(5) . ?
C52 O15 1.283(5) . ?
C53 O9 1.218(5) . ?
C53 O10 1.226(5) . ?
C54 O11 1.201(5) . ?
C54 O12 1.299(5) . ?
O1 H1 0.8200 . ?
O4 H4 0.8200 . ?
O6 H6 0.8200 . ?
O8 H8 0.8200 . ?
O12 H12 0.8200 . ?
O15 H15 0.8200 . ?
O17W H17A 0.8501 . ?
O17W H17B 0.8501 . ?
O18W H18A 0.8499 . ?
O18W H18B 0.8499 . ?
O19W H19A 0.8500 . ?
O19W H19B 0.8493 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 123.6(4) . . ?
N1 C1 H1A 118.2 . . ?
C2 C1 H1A 118.2 . . ?
C3 C2 C1 119.5(4) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 116.4(4) . . ?
C2 C3 C6 122.6(4) . . ?
C4 C3 C6 121.0(4) . . ?
C5 C4 C3 120.1(4) . . ?
C5 C4 H4A 120.0 . . ?
C3 C4 H4A 120.0 . . ?
N1 C5 C4 122.9(4) . . ?
N1 C5 H5 118.5 . . ?
C4 C5 H5 118.5 . . ?
C7 C6 C10 117.2(4) . . ?
C7 C6 C3 121.4(4) . . ?
C10 C6 C3 121.4(4) . . ?
C8 C7 C6 119.9(4) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
N2 C8 C7 121.4(4) . . ?
N2 C8 H8A 119.3 . . ?
C7 C8 H8A 119.3 . . ?
N2 C9 C10 120.6(4) . . ?
N2 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C9 C10 C6 120.8(4) . . ?
C9 C10 H10 119.6 . . ?
C6 C10 H10 119.6 . . ?
N2 C11 C12 109.2(3) . . ?
N2 C11 H11A 109.8 . . ?
C12 C11 H11A 109.8 . . ?
N2 C11 H11B 109.8 . . ?
C12 C11 H11B 109.8 . . ?
H11A C11 H11B 108.3 . . ?
C13 C12 C17 117.7(4) . . ?
C13 C12 C11 121.7(4) . . ?
C17 C12 C11 120.6(4) . . ?
C12 C13 C14 121.2(4) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C15 C14 C13 121.0(4) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C16 C15 C14 117.1(4) . . ?
C16 C15 C18 122.3(4) . . ?
C14 C15 C18 120.5(4) . . ?
C17 C16 C15 121.9(4) . . ?
C17 C16 H16 119.1 . . ?
C15 C16 H16 119.1 . . ?
C16 C17 C12 121.1(5) . . ?
C16 C17 H17 119.4 . . ?
C12 C17 H17 119.4 . . ?
C23 C18 C19 116.4(4) . . ?
C23 C18 C15 122.0(4) . . ?
C19 C18 C15 121.6(4) . . ?
C20 C19 C18 122.3(5) . . ?
C20 C19 H19 118.8 . . ?
C18 C19 H19 118.8 . . ?
C21 C20 C19 120.8(5) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C20 C21 C22 117.9(4) . . ?
C20 C21 C24 121.6(4) . . ?
C22 C21 C24 120.5(4) . . ?
C21 C22 C23 120.9(4) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 H22 119.6 . . ?
C18 C23 C22 121.7(4) . . ?
C18 C23 H23 119.2 . . ?
C22 C23 H23 119.2 . . ?
N3 C24 C21 109.9(4) . . ?
N3 C24 H24A 109.7 . . ?
C21 C24 H24A 109.7 . . ?
N3 C24 H24B 109.7 . . ?
C21 C24 H24B 109.7 . . ?
H24A C24 H24B 108.2 . . ?
N3 C25 C26 121.4(4) . . ?
N3 C25 H25 119.3 . . ?
C26 C25 H25 119.3 . . ?
C25 C26 C27 120.5(4) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C28 C27 C26 117.0(4) . . ?
C28 C27 C30 122.4(4) . . ?
C26 C27 C30 120.4(4) . . ?
C29 C28 C27 120.2(4) . . ?
C29 C28 H28 119.9 . . ?
C27 C28 H28 119.9 . . ?
N3 C29 C28 121.5(4) . . ?
N3 C29 H29 119.2 . . ?
C28 C29 H29 119.2 . . ?
C31 C30 C34 116.2(4) . . ?
C31 C30 C27 122.3(4) . . ?
C34 C30 C27 121.5(4) . . ?
C30 C31 C32 120.6(5) . . ?
C30 C31 H31 119.7 . . ?
C32 C31 H31 119.7 . . ?
N4 C32 C31 123.8(5) . . ?
N4 C32 H32 118.1 . . ?
C31 C32 H32 118.1 . . ?
N4 C33 C34 124.0(5) . . ?
N4 C33 H33 118.0 . . ?
C34 C33 H33 118.0 . . ?
C30 C34 C33 119.2(5) . . ?
C30 C34 H34 120.4 . . ?
C33 C34 H34 120.4 . . ?
C36 C35 C40 121.3(4) . . ?
C36 C35 H35 119.4 . . ?
C40 C35 H35 119.4 . . ?
C35 C36 C37 119.4(4) . . ?
C35 C36 C44 120.1(4) . . ?
C37 C36 C44 120.5(3) . . ?
C38 C37 C36 119.6(3) . . ?
C38 C37 C43 116.2(4) . . ?
C36 C37 C43 124.1(4) . . ?
C37 C38 C39 120.7(4) . . ?
C37 C38 H38 119.6 . . ?
C39 C38 H38 119.6 . . ?
C38 C39 C40 119.7(4) . . ?
C38 C39 C42 116.7(4) . . ?
C40 C39 C42 123.5(3) . . ?
C35 C40 C39 119.2(3) . . ?
C35 C40 C41 119.9(4) . . ?
C39 C40 C41 120.7(4) . . ?
O7 C41 O8 124.5(4) . . ?
O7 C41 C40 121.7(4) . . ?
O8 C41 C40 113.7(4) . . ?
O5 C42 O6 124.4(4) . . ?
O5 C42 C39 122.5(4) . . ?
O6 C42 C39 113.0(4) . . ?
O3 C43 O4 126.9(4) . . ?
O3 C43 C37 120.7(4) . . ?
O4 C43 C37 112.4(4) . . ?
O2 C44 O1 124.1(4) . . ?
O2 C44 C36 121.4(4) . . ?
O1 C44 C36 114.4(3) . . ?
C46 C45 C50 122.8(4) . . ?
C46 C45 H45 118.6 . . ?
C50 C45 H45 118.6 . . ?
C45 C46 C47 118.6(4) . . ?
C45 C46 C54 120.5(4) . . ?
C47 C46 C54 120.7(3) . . ?
C48 C47 C46 118.6(3) . . ?
C48 C47 C53 117.0(4) . . ?
C46 C47 C53 124.3(4) . . ?
C47 C48 C49 123.4(4) . . ?
C47 C48 H48 118.3 . . ?
C49 C48 H48 118.3 . . ?
C48 C49 C50 117.7(4) . . ?
C48 C49 C52 114.1(4) . . ?
C50 C49 C52 128.2(3) . . ?
C45 C50 C49 118.6(3) . . ?
C45 C50 C51 114.9(4) . . ?
C49 C50 C51 126.5(4) . . ?
O13 C51 O14 123.0(4) . . ?
O13 C51 C50 116.9(4) . . ?
O14 C51 C50 120.0(4) . . ?
O16 C52 O15 120.6(4) . . ?
O16 C52 C49 120.2(4) . . ?
O15 C52 C49 119.1(4) . . ?
O9 C53 O10 124.5(4) . . ?
O9 C53 C47 116.4(4) . . ?
O10 C53 C47 118.7(4) . . ?
O11 C54 O12 123.7(4) . . ?
O11 C54 C46 121.8(4) . . ?
O12 C54 C46 114.4(4) . . ?
C1 N1 C5 117.5(4) . . ?
C9 N2 C8 120.0(4) . . ?
C9 N2 C11 119.8(4) . . ?
C8 N2 C11 120.0(4) . . ?
C25 N3 C29 119.4(4) . . ?
C25 N3 C24 120.2(4) . . ?
C29 N3 C24 120.2(4) . . ?
C32 N4 C33 116.2(4) . . ?
C44 O1 H1 109.5 . . ?
C43 O4 H4 109.5 . . ?
C42 O6 H6 109.5 . . ?
C41 O8 H8 109.5 . . ?
C54 O12 H12 109.5 . . ?
C52 O15 H15 109.5 . . ?
H17A O17W H17B 108.3 . . ?
H18A O18W H18B 107.3 . . ?
H19A O19W H19B 104.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 0.9(8) . . . . ?
C1 C2 C3 C4 -1.2(7) . . . . ?
C1 C2 C3 C6 -178.9(4) . . . . ?
C2 C3 C4 C5 0.6(7) . . . . ?
C6 C3 C4 C5 178.3(4) . . . . ?
C3 C4 C5 N1 0.5(8) . . . . ?
C2 C3 C6 C7 26.1(6) . . . . ?
C4 C3 C6 C7 -151.4(4) . . . . ?
C2 C3 C6 C10 -156.2(4) . . . . ?
C4 C3 C6 C10 26.3(6) . . . . ?
C10 C6 C7 C8 -3.1(6) . . . . ?
C3 C6 C7 C8 174.7(4) . . . . ?
C6 C7 C8 N2 1.0(6) . . . . ?
N2 C9 C10 C6 -0.5(7) . . . . ?
C7 C6 C10 C9 2.9(6) . . . . ?
C3 C6 C10 C9 -174.9(4) . . . . ?
N2 C11 C12 C13 -118.0(5) . . . . ?
N2 C11 C12 C17 61.3(5) . . . . ?
C17 C12 C13 C14 -0.3(6) . . . . ?
C11 C12 C13 C14 179.0(4) . . . . ?
C12 C13 C14 C15 0.6(7) . . . . ?
C13 C14 C15 C16 -0.6(6) . . . . ?
C13 C14 C15 C18 177.7(4) . . . . ?
C14 C15 C16 C17 0.3(7) . . . . ?
C18 C15 C16 C17 -178.0(4) . . . . ?
C15 C16 C17 C12 0.0(7) . . . . ?
C13 C12 C17 C16 0.0(7) . . . . ?
C11 C12 C17 C16 -179.4(4) . . . . ?
C16 C15 C18 C23 -11.0(6) . . . . ?
C14 C15 C18 C23 170.7(4) . . . . ?
C16 C15 C18 C19 169.9(5) . . . . ?
C14 C15 C18 C19 -8.4(6) . . . . ?
C23 C18 C19 C20 -0.4(7) . . . . ?
C15 C18 C19 C20 178.7(5) . . . . ?
C18 C19 C20 C21 1.1(9) . . . . ?
C19 C20 C21 C22 -0.8(8) . . . . ?
C19 C20 C21 C24 -179.5(5) . . . . ?
C20 C21 C22 C23 0.0(7) . . . . ?
C24 C21 C22 C23 178.7(4) . . . . ?
C19 C18 C23 C22 -0.4(6) . . . . ?
C15 C18 C23 C22 -179.6(4) . . . . ?
C21 C22 C23 C18 0.7(7) . . . . ?
C20 C21 C24 N3 -51.4(6) . . . . ?
C22 C21 C24 N3 129.9(4) . . . . ?
N3 C25 C26 C27 -1.8(8) . . . . ?
C25 C26 C27 C28 -0.1(7) . . . . ?
C25 C26 C27 C30 177.0(4) . . . . ?
C26 C27 C28 C29 1.7(6) . . . . ?
C30 C27 C28 C29 -175.3(4) . . . . ?
C27 C28 C29 N3 -1.5(7) . . . . ?
C28 C27 C30 C31 -167.1(5) . . . . ?
C26 C27 C30 C31 16.1(7) . . . . ?
C28 C27 C30 C34 14.9(7) . . . . ?
C26 C27 C30 C34 -161.9(5) . . . . ?
C34 C30 C31 C32 3.1(8) . . . . ?
C27 C30 C31 C32 -175.0(5) . . . . ?
C30 C31 C32 N4 -1.7(10) . . . . ?
C31 C30 C34 C33 -2.4(8) . . . . ?
C27 C30 C34 C33 175.7(5) . . . . ?
N4 C33 C34 C30 0.1(9) . . . . ?
C40 C35 C36 C37 -0.4(6) . . . . ?
C40 C35 C36 C44 179.5(4) . . . . ?
C35 C36 C37 C38 1.4(6) . . . . ?
C44 C36 C37 C38 -178.6(4) . . . . ?
C35 C36 C37 C43 176.5(4) . . . . ?
C44 C36 C37 C43 -3.5(6) . . . . ?
C36 C37 C38 C39 -1.2(6) . . . . ?
C43 C37 C38 C39 -176.7(4) . . . . ?
C37 C38 C39 C40 0.2(6) . . . . ?
C37 C38 C39 C42 178.6(4) . . . . ?
C36 C35 C40 C39 -0.7(6) . . . . ?
C36 C35 C40 C41 -176.9(4) . . . . ?
C38 C39 C40 C35 0.8(6) . . . . ?
C42 C39 C40 C35 -177.5(4) . . . . ?
C38 C39 C40 C41 177.1(4) . . . . ?
C42 C39 C40 C41 -1.3(6) . . . . ?
C35 C40 C41 O7 167.9(4) . . . . ?
C39 C40 C41 O7 -8.4(6) . . . . ?
C35 C40 C41 O8 -9.4(6) . . . . ?
C39 C40 C41 O8 174.3(4) . . . . ?
C38 C39 C42 O5 -84.4(5) . . . . ?
C40 C39 C42 O5 93.9(5) . . . . ?
C38 C39 C42 O6 91.5(5) . . . . ?
C40 C39 C42 O6 -90.2(5) . . . . ?
C38 C37 C43 O3 90.2(5) . . . . ?
C36 C37 C43 O3 -85.1(6) . . . . ?
C38 C37 C43 O4 -87.0(5) . . . . ?
C36 C37 C43 O4 97.8(5) . . . . ?
C35 C36 C44 O2 174.5(4) . . . . ?
C37 C36 C44 O2 -5.6(7) . . . . ?
C35 C36 C44 O1 -8.0(6) . . . . ?
C37 C36 C44 O1 171.9(4) . . . . ?
C50 C45 C46 C47 -4.4(6) . . . . ?
C50 C45 C46 C54 171.5(4) . . . . ?
C45 C46 C47 C48 6.0(6) . . . . ?
C54 C46 C47 C48 -169.9(4) . . . . ?
C45 C46 C47 C53 -170.3(4) . . . . ?
C54 C46 C47 C53 13.8(6) . . . . ?
C46 C47 C48 C49 -2.5(6) . . . . ?
C53 C47 C48 C49 174.1(4) . . . . ?
C47 C48 C49 C50 -2.8(6) . . . . ?
C47 C48 C49 C52 177.0(4) . . . . ?
C46 C45 C50 C49 -0.9(6) . . . . ?
C46 C45 C50 C51 176.9(4) . . . . ?
C48 C49 C50 C45 4.4(6) . . . . ?
C52 C49 C50 C45 -175.3(4) . . . . ?
C48 C49 C50 C51 -173.1(4) . . . . ?
C52 C49 C50 C51 7.2(7) . . . . ?
C45 C50 C51 O13 -19.2(6) . . . . ?
C49 C50 C51 O13 158.3(4) . . . . ?
C45 C50 C51 O14 160.0(4) . . . . ?
C49 C50 C51 O14 -22.4(7) . . . . ?
C48 C49 C52 O16 14.4(6) . . . . ?
C50 C49 C52 O16 -165.9(4) . . . . ?
C48 C49 C52 O15 -162.8(4) . . . . ?
C50 C49 C52 O15 17.0(7) . . . . ?
C48 C47 C53 O9 53.8(6) . . . . ?
C46 C47 C53 O9 -129.8(5) . . . . ?
C48 C47 C53 O10 -119.3(5) . . . . ?
C46 C47 C53 O10 57.0(7) . . . . ?
C45 C46 C54 O11 -152.0(5) . . . . ?
C47 C46 C54 O11 23.8(7) . . . . ?
C45 C46 C54 O12 24.5(6) . . . . ?
C47 C46 C54 O12 -159.6(4) . . . . ?
C2 C1 N1 C5 0.2(8) . . . . ?
C4 C5 N1 C1 -0.8(8) . . . . ?
C10 C9 N2 C8 -1.7(6) . . . . ?
C10 C9 N2 C11 173.6(4) . . . . ?
C7 C8 N2 C9 1.5(6) . . . . ?
C7 C8 N2 C11 -173.9(4) . . . . ?
C12 C11 N2 C9 -104.6(4) . . . . ?
C12 C11 N2 C8 70.8(5) . . . . ?
C26 C25 N3 C29 2.1(7) . . . . ?
C26 C25 N3 C24 -173.2(4) . . . . ?
C28 C29 N3 C25 -0.4(6) . . . . ?
C28 C29 N3 C24 174.9(4) . . . . ?
C21 C24 N3 C25 95.6(5) . . . . ?
C21 C24 N3 C29 -79.6(5) . . . . ?
C31 C32 N4 C33 -0.6(9) . . . . ?
C34 C33 N4 C32 1.4(8) . . . . ?

_refine_diff_density_max         0.665
_refine_diff_density_min         -0.560
_refine_diff_density_rms         0.063



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 2372803'
loop_
_audit_author_name
_audit_author_address
'Yang Hua'
;Northeast Normal University
China
;
_audit_update_record             
;
2024-08-03 deposited with the CCDC.	2024-10-10 downloaded from the CCDC.
;
_audit_creation_date             2024-07-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H4 O8, C28 H24 N4, 3(H2 O)'
_chemical_formula_sum            'C38 H34 N4 O11'
_chemical_formula_weight         722.69
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.191(3)
_cell_length_b                   12.609(4)
_cell_length_c                   14.370(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.56(2)
_cell_angle_gamma                90
_cell_volume                     1660.0(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2929
_cell_measurement_temperature    294.96
_cell_measurement_theta_max      59.25
_cell_measurement_theta_min      4.67
_shelx_estimated_absorpt_T_max   0.840
_shelx_estimated_absorpt_T_min   0.813
_exptl_absorpt_coefficient_mu    0.901
_exptl_absorpt_correction_T_max  0.835
_exptl_absorpt_correction_T_min  0.806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1143 before and 0.0651 after correction.
The Ratio of minimum to maximum transmission is 0.8404.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             756
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0606
_diffrn_reflns_av_unetI/netI     0.0640
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8448
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        63.801
_diffrn_reflns_theta_max         63.801
_diffrn_reflns_theta_min         4.672
_diffrn_ambient_temperature      294.96
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1795
_reflns_number_total             2666
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         2666
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1004
_refine_ls_R_factor_gt           0.0602
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0770P)²+1.0822P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1489
_refine_ls_wR_factor_ref         0.1706
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Others
 Sof(O2WA)=Sof(H2WC)=Sof(H2WD)=1-FVAR(1)
 Sof(O2WB)=Sof(H2WA)=Sof(H2WB)=FVAR(1)
 Fixed Sof: O1W(0.5) H1WA(0.5) H1WB(0.5)
3.a Riding coordinates:
 O1W(H1WA,H1WB), O2WB(H2WA,H2WB), O2WA(H2WC,H2WD)
3.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
3.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C18(H18), C19(H19), C5(H5), C11(H11), C3(H3), C13(H13), C15(H15),
 C2(H2), C17(H17), C9(H9)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5961(2) 0.30538(19) 0.82913(16) 0.0576(7) Uani 1 1 d . . . . .
O4 O 0.4120(3) 0.67937(18) 0.80481(14) 0.0587(7) Uani 1 1 d . . . . .
O6 O 0.3569(2) 0.3279(2) 0.80972(17) 0.0735(8) Uani 1 1 d . . . . .
O3 O 0.4987(4) 0.5343(2) 0.74572(16) 0.0829(9) Uani 1 1 d . . . . .
C1 C 0.4923(3) 0.4309(2) 0.92364(17) 0.0285(6) Uani 1 1 d . . . . .
C4 C 0.4860(3) 0.6072(2) 0.98557(17) 0.0311(7) Uani 1 1 d . . . . .
H4 H 0.4763 0.6799 0.9760 0.037 Uiso 1 1 calc R U . . .
C6 C 0.4783(3) 0.5401(2) 0.90848(17) 0.0291(6) Uani 1 1 d . . . . .
N1 N 0.9629(3) 0.4633(2) 0.74429(18) 0.0524(8) Uani 1 1 d . . . . .
C8 C 0.4611(3) 0.5871(3) 0.81104(19) 0.0372(7) Uani 1 1 d . . . . .
C10 C 0.4753(3) 0.3509(2) 0.84661(19) 0.0369(7) Uani 1 1 d . . . . .
C12 C 0.9824(3) 0.4459(3) 0.9157(2) 0.0469(8) Uani 1 1 d . . . . .
N2 N 0.9626(4) 0.7879(3) 0.3439(2) 0.0724(9) Uani 1 1 d . . . . .
C14 C 0.9627(3) 0.6011(3) 0.5944(2) 0.0474(8) Uani 1 1 d . . . . .
C16 C 0.9626(4) 0.6680(3) 0.5091(2) 0.0506(9) Uani 1 1 d . . . . .
C18 C 1.1156(4) 0.4524(3) 0.9630(3) 0.0609(10) Uani 1 1 d . . . . .
H18 H 1.1954 0.4202 0.9389 0.073 Uiso 1 1 calc R U . . .
C19 C 1.0909(4) 0.5617(3) 0.6391(2) 0.0597(10) Uani 1 1 d . . . . .
H19 H 1.1801 0.5819 0.6183 0.072 Uiso 1 1 calc R U . . .
C5 C 1.0885(4) 0.4941(3) 0.7127(2) 0.0608(10) Uani 1 1 d . . . . .
H5 H 1.1761 0.4691 0.7414 0.073 Uiso 1 1 calc R U . . .
C11 C 0.8346(4) 0.6925(3) 0.4553(3) 0.0675(11) Uani 1 1 d . . . . .
H11 H 0.7453 0.6691 0.4737 0.081 Uiso 1 1 calc R U . . .
C3 C 0.8354(4) 0.5704(3) 0.6317(3) 0.0682(11) Uani 1 1 d . . . . .
H3 H 0.7466 0.5968 0.6061 0.082 Uiso 1 1 calc R U . . .
C13 C 1.0896(4) 0.7070(3) 0.4774(3) 0.0644(10) Uani 1 1 d . . . . .
H13 H 1.1786 0.6942 0.5110 0.077 Uiso 1 1 calc R U . . .
C7 C 0.9628(4) 0.3885(3) 0.8245(2) 0.0621(10) Uani 1 1 d . . . . .
H7A H 1.0411 0.3374 0.8208 0.075 Uiso 1 1 calc R U . . .
H7B H 0.8712 0.3499 0.8210 0.075 Uiso 1 1 calc R U . . .
C15 C 0.8376(4) 0.5021(3) 0.7054(3) 0.0673(11) Uani 1 1 d . . . . .
H15 H 0.7502 0.4824 0.7289 0.081 Uiso 1 1 calc R U . . .
C2 C 1.1341(4) 0.5063(3) 1.0466(3) 0.0646(11) Uani 1 1 d . . . . .
H2 H 1.2265 0.5104 1.0779 0.078 Uiso 1 1 calc R U . . .
C17 C 0.8400(5) 0.7512(3) 0.3750(3) 0.0723(11) Uani 1 1 d . . . . .
H17 H 0.7525 0.7661 0.3405 0.087 Uiso 1 1 calc R U . . .
C9 C 1.0847(5) 0.7650(3) 0.3958(3) 0.0707(11) Uani 1 1 d . . . . .
H9 H 1.1724 0.7895 0.3758 0.085 Uiso 1 1 calc R U . . .
O1W O 0.5253(8) 0.3684(4) 0.6041(4) 0.101(2) Uani 0.5 1 d . . P . .
H1WA H 0.5039 0.4320 0.6173 0.151 Uiso 0.5 1 d R U P . .
H1WB H 0.5912 0.3685 0.5658 0.151 Uiso 0.5 1 d R U P . .
H1 H 0.587(5) 0.258(4) 0.777(3) 0.107(15) Uiso 1 1 d . . . . .
O2WB O 0.4417(12) 0.6236(13) 0.5528(6) 0.099(5) Uani 0.39(2) 1 d . . P A 1
H2WA H 0.4545 0.5963 0.6069 0.149 Uiso 0.39(2) 1 d R U P A 1
H2WB H 0.3545 0.6072 0.5341 0.149 Uiso 0.39(2) 1 d R U P A 1
O2WA O 0.4207(8) 0.5333(15) 0.5585(4) 0.135(6) Uani 0.61(2) 1 d . . P A 2
H2WC H 0.4608 0.5421 0.6133 0.203 Uiso 0.61(2) 1 d R U P A 2
H2WD H 0.4738 0.5683 0.5237 0.203 Uiso 0.61(2) 1 d R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C10 1.292(3) . ?
O1 H1 0.95(5) . ?
O4 C8 1.249(4) . ?
O6 C10 1.207(3) . ?
O3 C8 1.222(4) . ?
C1 C4 1.390(3) 3_667 ?
C1 C6 1.398(4) . ?
C1 C10 1.497(4) . ?
C4 C1 1.390(3) 3_667 ?
C4 H4 0.9300 . ?
C4 C6 1.391(4) . ?
C6 C8 1.517(4) . ?
N1 C5 1.332(4) . ?
N1 C7 1.490(4) . ?
N1 C15 1.333(4) . ?
C12 C18 1.355(4) . ?
C12 C7 1.495(5) . ?
C12 C2 1.377(5) 3_767 ?
N2 C17 1.328(5) . ?
N2 C9 1.330(5) . ?
C14 C16 1.488(5) . ?
C14 C19 1.388(4) . ?
C14 C3 1.380(5) . ?
C16 C11 1.390(5) . ?
C16 C13 1.377(5) . ?
C18 H18 0.9300 . ?
C18 C2 1.379(5) . ?
C19 H19 0.9300 . ?
C19 C5 1.359(5) . ?
C5 H5 0.9300 . ?
C11 H11 0.9300 . ?
C11 C17 1.376(5) . ?
C3 H3 0.9300 . ?
C3 C15 1.363(5) . ?
C13 H13 0.9300 . ?
C13 C9 1.380(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C15 H15 0.9300 . ?
C2 C12 1.377(5) 3_767 ?
C2 H2 0.9300 . ?
C17 H17 0.9300 . ?
C9 H9 0.9300 . ?
O1W H1WA 0.8499 . ?
O1W H1WB 0.8499 . ?
O2WB H2WA 0.8499 . ?
O2WB H2WB 0.8501 . ?
O2WA H2WC 0.8500 . ?
O2WA H2WD 0.8501 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O1 H1 114(3) . . ?
C4 C1 C6 119.4(2) 3_667 . ?
C4 C1 C10 117.4(2) 3_667 . ?
C6 C1 C10 123.1(2) . . ?
C1 C4 H4 118.9 3_667 . ?
C1 C4 C6 122.1(2) 3_667 . ?
C6 C4 H4 118.9 . . ?
C1 C6 C8 122.0(2) . . ?
C4 C6 C1 118.4(2) . . ?
C4 C6 C8 119.5(2) . . ?
C5 N1 C7 120.2(3) . . ?
C5 N1 C15 119.5(3) . . ?
C15 N1 C7 120.3(3) . . ?
O4 C8 C6 116.1(3) . . ?
O3 C8 O4 125.1(3) . . ?
O3 C8 C6 118.8(3) . . ?
O1 C10 C1 113.7(2) . . ?
O6 C10 O1 124.5(3) . . ?
O6 C10 C1 121.6(3) . . ?
C18 C12 C7 120.7(3) . . ?
C18 C12 C2 118.4(3) . 3_767 ?
C2 C12 C7 120.9(3) 3_767 . ?
C17 N2 C9 115.8(3) . . ?
C19 C14 C16 122.0(3) . . ?
C3 C14 C16 122.2(3) . . ?
C3 C14 C19 115.7(3) . . ?
C11 C16 C14 121.9(3) . . ?
C13 C16 C14 122.0(3) . . ?
C13 C16 C11 116.1(3) . . ?
C12 C18 H18 119.6 . . ?
C12 C18 C2 120.8(3) . . ?
C2 C18 H18 119.6 . . ?
C14 C19 H19 119.4 . . ?
C5 C19 C14 121.3(3) . . ?
C5 C19 H19 119.4 . . ?
N1 C5 C19 121.1(3) . . ?
N1 C5 H5 119.5 . . ?
C19 C5 H5 119.5 . . ?
C16 C11 H11 120.0 . . ?
C17 C11 C16 120.1(4) . . ?
C17 C11 H11 120.0 . . ?
C14 C3 H3 119.4 . . ?
C15 C3 C14 121.2(3) . . ?
C15 C3 H3 119.4 . . ?
C16 C13 H13 120.0 . . ?
C16 C13 C9 119.9(3) . . ?
C9 C13 H13 120.0 . . ?
N1 C7 C12 111.3(3) . . ?
N1 C7 H7A 109.4 . . ?
N1 C7 H7B 109.4 . . ?
C12 C7 H7A 109.4 . . ?
C12 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
N1 C15 C3 121.1(3) . . ?
N1 C15 H15 119.4 . . ?
C3 C15 H15 119.4 . . ?
C12 C2 C18 120.8(3) 3_767 . ?
C12 C2 H2 119.6 3_767 . ?
C18 C2 H2 119.6 . . ?
N2 C17 C11 124.0(4) . . ?
N2 C17 H17 118.0 . . ?
C11 C17 H17 118.0 . . ?
N2 C9 C13 124.2(4) . . ?
N2 C9 H9 117.9 . . ?
C13 C9 H9 117.9 . . ?
H1WA O1W H1WB 109.5 . . ?
H2WA O2WB H2WB 104.5 . . ?
H2WC O2WA H2WD 104.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C4 C6 C1 0.3(4) 3_667 . . . ?
C1 C4 C6 C8 -177.3(2) 3_667 . . . ?
C1 C6 C8 O4 161.8(3) . . . . ?
C1 C6 C8 O3 -19.8(4) . . . . ?
C4 C1 C6 C4 -0.3(4) 3_667 . . . ?
C4 C1 C6 C8 177.2(2) 3_667 . . . ?
C4 C1 C10 O1 -74.5(3) 3_667 . . . ?
C4 C1 C10 O6 101.1(3) 3_667 . . . ?
C4 C6 C8 O4 -20.7(4) . . . . ?
C4 C6 C8 O3 157.7(3) . . . . ?
C6 C1 C10 O1 109.6(3) . . . . ?
C6 C1 C10 O6 -74.8(4) . . . . ?
C10 C1 C6 C4 175.6(2) . . . . ?
C10 C1 C6 C8 -6.9(4) . . . . ?
C12 C18 C2 C12 0.5(6) . . . 3_767 ?
C14 C16 C11 C17 -177.5(3) . . . . ?
C14 C16 C13 C9 177.2(3) . . . . ?
C14 C19 C5 N1 0.1(6) . . . . ?
C14 C3 C15 N1 0.5(6) . . . . ?
C16 C14 C19 C5 -175.0(3) . . . . ?
C16 C14 C3 C15 174.7(3) . . . . ?
C16 C11 C17 N2 -0.2(6) . . . . ?
C16 C13 C9 N2 0.7(6) . . . . ?
C18 C12 C7 N1 -97.8(4) . . . . ?
C19 C14 C16 C11 168.8(3) . . . . ?
C19 C14 C16 C13 -9.3(5) . . . . ?
C19 C14 C3 C15 -2.6(5) . . . . ?
C5 N1 C7 C12 84.8(4) . . . . ?
C5 N1 C15 C3 2.1(6) . . . . ?
C11 C16 C13 C9 -1.0(5) . . . . ?
C3 C14 C16 C11 -8.3(5) . . . . ?
C3 C14 C16 C13 173.6(3) . . . . ?
C3 C14 C19 C5 2.3(5) . . . . ?
C13 C16 C11 C17 0.8(5) . . . . ?
C7 N1 C5 C19 179.5(3) . . . . ?
C7 N1 C15 C3 -179.8(3) . . . . ?
C7 C12 C18 C2 179.3(3) . . . . ?
C15 N1 C5 C19 -2.4(5) . . . . ?
C15 N1 C7 C12 -93.3(4) . . . . ?
C2 C12 C18 C2 -0.5(6) 3_767 . . . ?
C2 C12 C7 N1 82.0(4) 3_767 . . . ?
C17 N2 C9 C13 0.0(6) . . . . ?
C9 N2 C17 C11 -0.2(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_y1
_database_code_depnum_ccdc_archive 'CCDC 2372809'
loop_
_audit_author_name
_audit_author_address
'Yang Hua'
;Northeast Normal University
China
;
_audit_update_record             
;
2024-08-03 deposited with the CCDC.	2024-10-10 downloaded from the CCDC.
;
_audit_creation_date             2024-07-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C10 H4 O8), C22 H22 N4'
_chemical_formula_sum            'C42 H30 N4 O16'
_chemical_formula_weight         846.70
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0044(2)
_cell_length_b                   9.6508(2)
_cell_length_c                   12.8662(3)
_cell_angle_alpha                71.2430(10)
_cell_angle_beta                 73.9480(10)
_cell_angle_gamma                73.0770(10)
_cell_volume                     881.82(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    5462
_cell_measurement_temperature    284.0
_cell_measurement_theta_max      66.75
_cell_measurement_theta_min      3.70
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.060
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             438
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11686
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        66.855
_diffrn_reflns_theta_max         66.855
_diffrn_reflns_theta_min         3.704
_diffrn_ambient_temperature      284.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2637
_reflns_number_total             3117
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3117
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0429
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0625P)²+0.4785P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1164
_refine_ls_wR_factor_ref         0.1235
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C19(H19), N1(H1), C14(H14), C2(H2), C7(H7), C8(H8), C9(H9), C10(H10), C1(H1A),
  C4(H4), C5(H5)
2.c Idealised tetrahedral OH refined as rotating group:
 O6(H6), O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O8 O 0.6179(2) 1.38665(14) 0.27581(13) 0.0390(4) Uani 1 1 d . . . . .
O6 O 0.64569(19) 1.31747(16) -0.02543(12) 0.0383(4) Uani 1 1 d . . . . .
H6 H 0.6053 1.3904 -0.0729 0.057 Uiso 1 1 calc R U . . .
O3 O 0.55509(19) 0.66112(15) 0.26181(14) 0.0403(4) Uani 1 1 d . . . . .
H3 H 0.5855 0.5712 0.2654 0.060 Uiso 1 1 calc R U . . .
O5 O 0.38570(19) 1.25576(17) 0.00372(13) 0.0413(4) Uani 1 1 d . . . . .
O7 O 0.4189(2) 1.43025(15) 0.17063(13) 0.0411(4) Uani 1 1 d . . . . .
O4 O 0.8479(2) 0.65058(16) 0.20826(14) 0.0447(4) Uani 1 1 d . . . . .
O2 O 0.7654(3) 0.8423(2) 0.50393(13) 0.0542(5) Uani 1 1 d . . . . .
N2 N 1.0089(2) -0.31175(17) 0.89784(14) 0.0298(4) Uani 1 1 d . . . . .
O1 O 0.6920(3) 0.67885(18) 0.44516(17) 0.0694(6) Uani 1 1 d . . . . .
C20 C 0.5675(2) 1.13546(19) 0.13977(15) 0.0237(4) Uani 1 1 d . . . . .
C12 C 0.5357(2) 1.34677(19) 0.22442(15) 0.0263(4) Uani 1 1 d . . . . .
C19 C 0.6033(2) 0.9838(2) 0.14710(16) 0.0270(4) Uani 1 1 d . . . . .
H19 H 0.5945 0.9533 0.0876 0.032 Uiso 1 1 calc R U . . .
C22 C 0.5807(2) 1.18242(19) 0.22914(15) 0.0236(4) Uani 1 1 d . . . . .
N1 N 0.7753(3) 0.4105(2) 0.55484(17) 0.0468(5) Uani 1 1 d . . . . .
H1 H 0.7513 0.5004 0.5128 0.056 Uiso 1 1 calc R U . . .
C21 C 0.5198(2) 1.24485(19) 0.03357(15) 0.0265(4) Uani 1 1 d . . . . .
C15 C 0.6664(2) 0.92194(19) 0.33156(15) 0.0260(4) Uani 1 1 d . . . . .
C17 C 0.6522(2) 0.87628(19) 0.24195(16) 0.0264(4) Uani 1 1 d . . . . .
C14 C 0.6313(2) 1.07412(19) 0.32333(15) 0.0260(4) Uani 1 1 d . . . . .
H14 H 0.6418 1.1046 0.3824 0.031 Uiso 1 1 calc R U . . .
C6 C 0.8970(2) -0.0304(2) 0.76281(16) 0.0285(4) Uani 1 1 d . . . . .
C18 C 0.6947(3) 0.7146(2) 0.23939(17) 0.0304(4) Uani 1 1 d . . . . .
C16 C 0.7141(3) 0.8076(2) 0.43726(17) 0.0336(4) Uani 1 1 d . . . . .
C2 C 0.8792(3) 0.2437(2) 0.71384(18) 0.0373(5) Uani 1 1 d . . . . .
H2 H 0.9245 0.2279 0.7769 0.045 Uiso 1 1 calc R U . . .
C7 C 0.9182(3) -0.0503(2) 0.87090(17) 0.0345(5) Uani 1 1 d . . . . .
H7 H 0.8944 0.0328 0.8987 0.041 Uiso 1 1 calc R U . . .
C3 C 0.8509(2) 0.1235(2) 0.68921(16) 0.0300(4) Uani 1 1 d . . . . .
C8 C 0.9737(3) -0.1910(2) 0.93657(17) 0.0347(5) Uani 1 1 d . . . . .
H8 H 0.9871 -0.2027 1.0087 0.042 Uiso 1 1 calc R U . . .
C9 C 0.9817(3) -0.2976(2) 0.79622(18) 0.0366(5) Uani 1 1 d . . . . .
H9 H 1.0020 -0.3829 0.7717 0.044 Uiso 1 1 calc R U . . .
C10 C 0.9244(3) -0.1588(2) 0.72795(18) 0.0367(5) Uani 1 1 d . . . . .
H10 H 0.9040 -0.1508 0.6583 0.044 Uiso 1 1 calc R U . . .
C11 C 1.0761(3) -0.4624(2) 0.96910(18) 0.0342(5) Uani 1 1 d . . . . .
H11A H 1.1346 -0.4525 1.0223 0.041 Uiso 1 1 calc R U . . .
H11B H 1.1628 -0.5231 0.9227 0.041 Uiso 1 1 calc R U . . .
C1 C 0.8404(3) 0.3861(2) 0.6450(2) 0.0431(5) Uani 1 1 d . . . . .
H1A H 0.8600 0.4662 0.6618 0.052 Uiso 1 1 calc R U . . .
C4 C 0.7836(3) 0.1519(2) 0.59359(18) 0.0388(5) Uani 1 1 d . . . . .
H4 H 0.7640 0.0741 0.5740 0.047 Uiso 1 1 calc R U . . .
C5 C 0.7465(3) 0.2979(3) 0.5283(2) 0.0477(6) Uani 1 1 d . . . . .
H5 H 0.7005 0.3179 0.4647 0.057 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O8 C12 1.253(2) . ?
O6 H6 0.8200 . ?
O6 C21 1.315(2) . ?
O3 H3 0.8200 . ?
O3 C18 1.289(2) . ?
O5 C21 1.203(2) . ?
O7 C12 1.250(2) . ?
O4 C18 1.222(3) . ?
O2 C16 1.215(3) . ?
N2 C8 1.338(3) . ?
N2 C9 1.342(3) . ?
N2 C11 1.485(2) . ?
O1 C16 1.273(3) . ?
C20 C19 1.384(2) . ?
C20 C22 1.403(2) . ?
C20 C21 1.501(2) . ?
C12 C22 1.506(2) . ?
C19 H19 0.9300 . ?
C19 C17 1.390(3) . ?
C22 C14 1.391(2) . ?
N1 H1 0.8600 . ?
N1 C1 1.326(3) . ?
N1 C5 1.334(3) . ?
C15 C17 1.402(3) . ?
C15 C14 1.387(2) . ?
C15 C16 1.513(3) . ?
C17 C18 1.506(2) . ?
C14 H14 0.9300 . ?
C6 C7 1.393(3) . ?
C6 C3 1.486(3) . ?
C6 C10 1.389(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.388(3) . ?
C2 C1 1.376(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.369(3) . ?
C3 C4 1.394(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C9 C10 1.372(3) . ?
C10 H10 0.9300 . ?
C11 C11 1.500(4) 2_747 ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C1 H1A 0.9300 . ?
C4 H4 0.9300 . ?
C4 C5 1.382(3) . ?
C5 H5 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C21 O6 H6 109.5 . . ?
C18 O3 H3 109.5 . . ?
C8 N2 C9 120.51(17) . . ?
C8 N2 C11 119.37(16) . . ?
C9 N2 C11 120.11(17) . . ?
C19 C20 C22 119.82(16) . . ?
C19 C20 C21 118.01(15) . . ?
C22 C20 C21 122.16(15) . . ?
O8 C12 C22 116.76(16) . . ?
O7 C12 O8 126.17(16) . . ?
O7 C12 C22 117.07(16) . . ?
C20 C19 H19 119.4 . . ?
C20 C19 C17 121.11(16) . . ?
C17 C19 H19 119.4 . . ?
C20 C22 C12 120.54(15) . . ?
C14 C22 C20 118.72(16) . . ?
C14 C22 C12 120.71(15) . . ?
C1 N1 H1 119.5 . . ?
C1 N1 C5 121.01(19) . . ?
C5 N1 H1 119.5 . . ?
O6 C21 C20 112.55(15) . . ?
O5 C21 O6 124.62(17) . . ?
O5 C21 C20 122.65(17) . . ?
C17 C15 C16 120.78(16) . . ?
C14 C15 C17 118.99(16) . . ?
C14 C15 C16 120.21(17) . . ?
C19 C17 C15 119.56(16) . . ?
C19 C17 C18 116.73(16) . . ?
C15 C17 C18 123.66(16) . . ?
C22 C14 H14 119.1 . . ?
C15 C14 C22 121.80(17) . . ?
C15 C14 H14 119.1 . . ?
C7 C6 C3 119.94(17) . . ?
C10 C6 C7 117.26(17) . . ?
C10 C6 C3 122.78(18) . . ?
O3 C18 C17 113.38(16) . . ?
O4 C18 O3 125.71(17) . . ?
O4 C18 C17 120.56(17) . . ?
O2 C16 O1 126.9(2) . . ?
O2 C16 C15 120.96(18) . . ?
O1 C16 C15 112.12(18) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 120.0(2) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 C6 120.56(19) . . ?
C8 C7 H7 119.7 . . ?
C2 C3 C6 119.61(18) . . ?
C2 C3 C4 118.15(18) . . ?
C4 C3 C6 122.22(18) . . ?
N2 C8 C7 120.53(18) . . ?
N2 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
N2 C9 H9 119.5 . . ?
N2 C9 C10 120.90(18) . . ?
C10 C9 H9 119.5 . . ?
C6 C10 H10 120.0 . . ?
C9 C10 C6 120.04(19) . . ?
C9 C10 H10 120.0 . . ?
N2 C11 C11 109.79(19) . 2_747 ?
N2 C11 H11A 109.7 . . ?
N2 C11 H11B 109.7 . . ?
C11 C11 H11A 109.7 2_747 . ?
C11 C11 H11B 109.7 2_747 . ?
H11A C11 H11B 108.2 . . ?
N1 C1 C2 120.7(2) . . ?
N1 C1 H1A 119.6 . . ?
C2 C1 H1A 119.6 . . ?
C3 C4 H4 120.6 . . ?
C5 C4 C3 118.9(2) . . ?
C5 C4 H4 120.6 . . ?
N1 C5 C4 121.2(2) . . ?
N1 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O8 C12 C22 C20 -149.71(18) . . . . ?
O8 C12 C22 C14 32.1(3) . . . . ?
O7 C12 C22 C20 30.9(3) . . . . ?
O7 C12 C22 C14 -147.27(18) . . . . ?
N2 C9 C10 C6 1.2(3) . . . . ?
C20 C19 C17 C15 -0.3(3) . . . . ?
C20 C19 C17 C18 -177.78(17) . . . . ?
C20 C22 C14 C15 -0.9(3) . . . . ?
C12 C22 C14 C15 177.35(17) . . . . ?
C19 C20 C22 C12 -177.72(16) . . . . ?
C19 C20 C22 C14 0.5(3) . . . . ?
C19 C20 C21 O6 -110.00(19) . . . . ?
C19 C20 C21 O5 65.4(3) . . . . ?
C19 C17 C18 O3 -80.8(2) . . . . ?
C19 C17 C18 O4 92.8(2) . . . . ?
C22 C20 C19 C17 0.1(3) . . . . ?
C22 C20 C21 O6 68.5(2) . . . . ?
C22 C20 C21 O5 -116.2(2) . . . . ?
C21 C20 C19 C17 178.58(16) . . . . ?
C21 C20 C22 C12 3.8(3) . . . . ?
C21 C20 C22 C14 -177.93(17) . . . . ?
C15 C17 C18 O3 101.9(2) . . . . ?
C15 C17 C18 O4 -84.5(3) . . . . ?
C17 C15 C14 C22 0.6(3) . . . . ?
C17 C15 C16 O2 163.4(2) . . . . ?
C17 C15 C16 O1 -17.2(3) . . . . ?
C14 C15 C17 C19 0.0(3) . . . . ?
C14 C15 C17 C18 177.26(17) . . . . ?
C14 C15 C16 O2 -18.4(3) . . . . ?
C14 C15 C16 O1 161.1(2) . . . . ?
C6 C7 C8 N2 0.1(3) . . . . ?
C6 C3 C4 C5 -179.0(2) . . . . ?
C16 C15 C17 C19 178.21(17) . . . . ?
C16 C15 C17 C18 -4.5(3) . . . . ?
C16 C15 C14 C22 -177.61(17) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C7 C6 C3 C2 18.6(3) . . . . ?
C7 C6 C3 C4 -163.0(2) . . . . ?
C7 C6 C10 C9 -4.3(3) . . . . ?
C3 C6 C7 C8 -175.05(18) . . . . ?
C3 C6 C10 C9 174.36(19) . . . . ?
C3 C2 C1 N1 0.2(3) . . . . ?
C3 C4 C5 N1 0.6(4) . . . . ?
C8 N2 C9 C10 2.7(3) . . . . ?
C8 N2 C11 C11 96.1(3) . . . 2_747 ?
C9 N2 C8 C7 -3.4(3) . . . . ?
C9 N2 C11 C11 -83.1(3) . . . 2_747 ?
C10 C6 C7 C8 3.6(3) . . . . ?
C10 C6 C3 C2 -160.0(2) . . . . ?
C10 C6 C3 C4 18.4(3) . . . . ?
C11 N2 C8 C7 177.48(18) . . . . ?
C11 N2 C9 C10 -178.16(19) . . . . ?
C1 N1 C5 C4 -0.1(4) . . . . ?
C1 C2 C3 C6 178.67(19) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C5 N1 C1 C2 -0.3(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
